Gold(I)-Catalyzed Addition of Thiols and Thioacids to 3,3-Disubstituted Cyclopropenes

Abstract

Gold­(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold­(I) catalysts shows Echavarren’s cationic gold­(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway